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Synthesis of the tetrasaccharide α-D-Glcp-(1→3)-α-D-Manp-(1→2)-α-D-Manp-(1→2)-α-D-Manp recognised by Calreticulin/Calnexin
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2005 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 340, no 16, 2558-2562 p.Article in journal (Refereed) Published
Abstract [en]

The title compound as its methyl glycoside was efficiently synthesized using a block synthesis approach. Halide-assisted glycosidations between 6-O-acetyl-2,3,4-tri-O-benzyl-α-d-glucopyranosyl iodide and ethyl 2-O-acetyl-4,6-di-O-benzyl-1-thio-α-d-mannopyranoside using triphenylphosphine oxide as promoter yielded, with complete α-selectivity, a disaccharide building block in high yield. The perbenzylated derivative of this proved to be an excellent donor affording 88% of the protected target tetrasaccharide in an NIS/AgOTf-promoted coupling to a known methyl dimannoside acceptor. Deprotection through catalytic hydrogenolysis then gave the target compound in 47% overall yield.

Place, publisher, year, edition, pages
Elsevier Ltd , 2005. Vol. 340, no 16, 2558-2562 p.
Keyword [en]
Calreticulin substrates; Iodide glycosyl donors; Triphenylphosphine oxide promotion; Thioglycoside block donor
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-23721DOI: 10.1016/j.carres.2005.09.001OAI: oai:DiVA.org:su-23721DiVA: diva2:194157
Note
Part of urn:nbn:se:su:diva-459Available from: 2005-04-18 Created: 2005-04-18 Last updated: 2017-12-13Bibliographically approved
In thesis
1. Synthesis of Oligosaccharides for Interaction Studies with Various Lectins
Open this publication in new window or tab >>Synthesis of Oligosaccharides for Interaction Studies with Various Lectins
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

In this thesis, the syntheses of oligosaccharides for interaction studies with various lectins are described. The first section reports the syntheses of tetra, tri- and disaccharides corresponding to truncated versions of the glucosylated arm of Glc1Man9(GlcNAc)2, found in the biosynthesis of N-glycans. The thermodynamic parameters of their interaction with calreticulin, a lectin assisting and promoting the correct folding of newly synthesised glycoproteins, were established by isothermal titration calorimetry. In the second section, a new synthetic pathway leading to the same tetra- and trisaccharides is discussed. Adoption of a convergent strategy and of a different protecting group pattern resulted in significantly increased yields of the target structures. The third section describes the syntheses of a number of monodeoxy-trisaccharides related to the above trisaccharide Glc-α-(1→3)-Man-α-(1→2)-Man-α-OMe. Differentsynthetic approaches were explored and the choice of early introduction of the deoxy functionality proved the most beneficial. In the last section, the synthesis of spacer-linked LacNAc dimers as substrates for the lectins galectin-1 and -3 is presented. This synthesis was realized by glycosidation of a number diols with peracetylated LacNAc-oxazoline. Pyridinium triflate was tested as a new promoter, affording the target dimers in high yields. This promoter in combination with microwave irradiation gave even higher yields and also shortened the reaction times.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2005. 60 p.
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-459 (URN)91-7155-051-8 (ISBN)
Public defence
2005-05-13, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Opponent
Supervisors
Available from: 2005-04-18 Created: 2005-04-18Bibliographically approved

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